Reacción #95268

Ecuación de reacción

15-(tert-butoxy)-9-oxoprostanoic acid, ethyl ester

trifluoroacetic acid

→

15-hydroxy-9-oxoprostanoic acid, ethyl ester

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis then poured into 500 ml
2. 2
   Extracciónof ice water and extracted several times with chloroform
3. 3
   LavadoThe combined chloroform extracts are washed with saturated sodium bicarbonate solution, saturated sodium chloride solution
4. 4
   Secadodried with anhydrous magnesium sulfate
5. 5
   workup.DISSOLUTIONThe resulting oil is dissolved in 200 ml
6. 6
   workup.DISSOLUTIONThe residual oil is dissolved in chloroform
7. 7
   Lavadowashed with 1 N hydrochloric acid, saturated sodium chloride solution
8. 8
   Otrodried
9. 9
   Otroto give 21.7 g
10. 10
    Otrono uv absorption

Procedimiento

A solution of 25 g. of 15-(tert-butoxy)-9-oxoprostanoic acid, ethyl ester in 100 ml. of trifluoroacetic acid is stirred in an ice bath for 1 hour and is then poured into 500 ml. of ice water and extracted several times with chloroform. The combined chloroform extracts are washed with saturated sodium bicarbonate solution, saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and taken to dryness. The resulting oil is dissolved in 200 ml. of 1 N ammonium hydroxide in ethanol, kept at ambient temperature for 15 minutes, then taken to dryness. The residual oil is dissolved in chloroform and washed with 1 N hydrochloric acid, saturated sodium chloride solution, dried and taken to dryness to give 21.7 g. (100%) of product as a yellow syrup. There is essentially no uv absorption; λmaxKBr 2.90, 5.75, 8.45μ; nmr 2H quartet δ4.13 (OCH2 of ester), 1H broad singlet 3.63 (carbinolic proton), 3H triplet (CH3 of ester), and 3H distorted triplet 0.92 (terminal methyl); mass spectrum: m/e 368.

Fuente